Chestertown, Maryland Homes For Sale & Real Estate
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Real Estate Homes For Sale In Chestertown, MD
![Beautifully maintained home tucked away on a quiet cul-de-sac but still within walking distance to downtown shops, restaurants, and riverfront. Open floor plan with 9ft ceilings in the living room. 3 bedrooms and 2 full bath with a 2 car attached....](https://lh.rdcpix.com/5069eb953b1e1328ea06e5c2be8711b4l-f1338212051x.jpg)
$530,000 | Active Home listing
3 Beds | 2 Baths | 1,467 Sqft | 0 Acres Lot
217 RADCLIFFE DRIVE, CHESTERTOWN, MD 21620 KENT County
![Looking for extra space? This home has a large extra room that could be a primary bedroom & bath with walk in closet, a den/playroom, office with a separate private entrance, gym or whatever your lifestyle is in need of! The original primary....](https://lh.rdcpix.com/c8b620128f2cea068acba0f5be12dca2l-f3577804735x.jpg)
$284,000 | Active Home listing
4 Beds | 3 Baths | 1,632 Sqft | 1 Acres Lot
305 LINCOLN DRIVE, CHESTERTOWN, MD 21620 KENT County
![Investor Alert! A rare opportunity to own a piece of History in down town Chestertown! This home has been a very lucrative rental for the past 10 years which you can easily add to your portfolio or rennovate and bring it back to its glory! One of....](https://lh.rdcpix.com/4b5e769a6571b65b7996be5c40735f3el-f2855909224x.jpg)
$272,500 | Active Home listing
3 Beds | 2 Baths | 1,234 Sqft | 0 Acres Lot
631 HIGH STREET, CHESTERTOWN, MD 21620 KENT County
![Discover your dream home nestled in a serene water-privileged community with exclusive access to a boat ramp, a small marina, and picturesque walking trails. This inviting 3-bedroom, 2-bath residence offers an ideal blend of comfort, convenience,....](https://lh.rdcpix.com/74525d3d5b0ec6f724cb89f666a2168al-f1527441151x.jpg)
$359,000 | Active Home listing
3 Beds | 2 Baths | 1,789 Sqft | 1 Acres Lot
23120 CLUB TERRACE, CHESTERTOWN, MD 21620 KENT County
![This beautiful custom home on an acre of land has 4 Beds and 2.5 baths. There is an eat-in-Kitchen with granite countertops that is completed by the Maple Wood Island, Gas cooking, and stainless steel appliances, soft close cabinets and 2....](https://lh.rdcpix.com/316e019bb6c92e5064f4a7b55255eda8l-f2458391958x.jpg)
$450,000 | Active Home listing
4 Beds | 3 Baths | 2,240 Sqft | 1 Acres Lot
8500 BROAD NECK ROAD SW, CHESTERTOWN, MD 21620 KENT County
![Looking for something truly special? Don't miss this unique offering, located in the vibrant heart of Chestertown's Historic and Arts & Entertainment Districts!
Boasting a legacy of over half a century under the stewardship of one devoted family,....](https://lh.rdcpix.com/53a8f6613b5fde98048e0fd0b2c4143fl-f3524810863x.jpg)
$425,000 | Active Home listing
7 Beds | 4 Baths | 3,664 Sqft | 0 Acres Lot
349 HIGH STREET, CHESTERTOWN, MD 21620 KENT County
![Well maintained Cape Cod in the sought after Coventry Farms subdivision in Chestertown - 1st Floor Master Bedroom includes a spacious walk in closet and a large Full Bath with Walk in Shower – 4 bedrooms, 2.5 baths, a spacious living room, and a....](https://lh.rdcpix.com/4bd03319eb8673aa31d64d5dbef23320l-f3984066429x.jpg)
$360,000 | Active Home listing
4 Beds | 3 Baths | 2,472 Sqft | 0 Acres Lot
213 DEVON DRIVE, CHESTERTOWN, MD 21620 KENT County
![Welcome to a captivating opportunity to reside in the idyllic neighborhood of The Grove in picturesque Queen Anne's County. Prepare to be enchanted by this charming abode, where every detail exudes warmth and comfort.
Step inside and be greeted....](https://lh.rdcpix.com/ed1a3b94b3c8fa049be3e50b171bea0al-f1032865805x.jpg)
$515,000 | Active Home listing
4 Beds | 3 Baths | 2,864 Sqft | 1 Acres Lot
112 SHEAFFER ROAD, CHESTERTOWN, MD 21620 QUEEN ANNES County
![Step inside this stately brick colonial to see and feel the quality of this stunning renovation in Chestertown's vibrant historic district! From the five piece luxury bath in the owner's suite, to the full guest apartment on the third floor, no....](https://lh.rdcpix.com/87ae5b44dacc4d998f03bae5b73693dbl-f2434788026x.jpg)
$879,000 | Active Home listing
4 Beds | 4 Baths | 3,355 Sqft | 0 Acres Lot
307 WASHINGTON AVENUE, CHESTERTOWN, MD 21620 KENT County
![This circa 2011, white brick house was built to celebrate the expansive views over the Chester River Yacht &Country Club golf course to the Chester River. There is an attractive patio at one end and a screened porch off the owner's suite. The....](https://lh.rdcpix.com/0f9525e93295054276c0ced6ddf21297l-f2172110196x.jpg)
$975,000 | Active Home listing
4 Beds | 3 Baths | 4,730 Sqft | 1 Acres Lot
7755 WATERVIEW LANE, CHESTERTOWN, MD 21620 KENT County
![Wonderful renovation, modern, efficient, and move in ready! Home features vaulted ceilings with open flexible floorplan and 2 brand new luxury bathrooms. Energy efficient instant hot water heater. Large side deck, plenty of parking, small....](https://lh.rdcpix.com/25cf984a1506c7cc1e31e6fe1385f0cel-f2312242758x.jpg)
$289,000 | Active Home listing
2 Beds | 2 Baths | 864 Sqft | 1 Acres Lot
235 BURCHARD SAWMILL ROAD, CHESTERTOWN, MD 21620 QUEEN ANNES County
![Step into a world of timeless elegance and tranquility with this meticulously maintained retreat. As you turn into the Fairgale Subdivision, it feels as though you are entering an estate, with majestic trees lining both sides of the paved road,....](https://lh.rdcpix.com/7fb4bab1aefe55724ed99015c6413660l-f2672713285x.jpg)
$1,300,000 | Active Home listing
5 Beds | 5 Baths | 6,459 Sqft | 4 Acres Lot
22956 FAIRGALE FARM LANE, CHESTERTOWN, MD 21620 KENT County
![Well maintained 2 bedroom 1 bath Colonial on .69 acres with winter water views of Fishing Creek! Features Include: Screened Porch * 1-Car Attached Garage * Tilt-in Insulated Double Pane Windows * Large Living / Dining Room Combo with Brick....](https://lh.rdcpix.com/e6bcba5a67d6a5a80593cb338aa760d4l-f4034178943x.jpg)
$269,900 | Active Home listing
2 Beds | 1 Baths | 1,408 Sqft | 1 Acres Lot
332 TRUSLOW ROAD, CHESTERTOWN, MD 21620 QUEEN ANNES County
![Welcome to your tranquil retreat at Orchard Hill, where modern sophistication meets peaceful living on 1.89 acres of beautifully landscaped grounds. This stunning Cape Cod style home offers an abundance of amenities and thoughtful details....](https://lh.rdcpix.com/3bf0c34af79541304cfae63fcb05c7e0l-f268917998x.jpg)
$498,000 | Active Home listing
2 Beds | 3 Baths | 2,210 Sqft | 2 Acres Lot
8757 ORCHARD DRIVE, CHESTERTOWN, MD 21620 KENT County
![Price improvement! Two perfectly adorable cottages in Tolchester. Both were completely remodeled. The cottages sit on 3 lots totaling about .46 acres. Each has one bedroom, a full bath, kitchen and living areas. The front cottage also has an....](https://lh.rdcpix.com/c0d8765dba97071117068f00d66a0c91l-f1647933777x.jpg)
$279,900 | Active Home listing
2 Beds | 2 Baths | 1,150 Sqft | 0 Acres Lot
9020 CUMBERLAND STREET, CHESTERTOWN, MD 21620 KENT County
![SMITH-RINGGOLD HOUSE. ca. 1750
OWNER IS MEETING THE MARKET for this rare property WITH PRICE NOW AT $1,6500,000.
This exceptional property is a rare find: an authentic waterfront 18th century home with 21st century comfort in heart of....](https://lh.rdcpix.com/2705e33ce1dc4bfa7d308ffcc63e0653l-f2537052481x.jpg)
$1,650,000 | Active Home listing
4 Beds | 5 Baths | 5,195 Sqft | 0 Acres Lot
201 N WATER STREET, CHESTERTOWN, MD 21620 KENT County
Chestertown, MD Real Estate Home Trends
Kent County Buy Statistics
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Chestertown Types of Homes for Sale
Chestertown Real Estate Listings
Chestertown, MD Homes Prices
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Real Estate Home Mortgage Loan Rates Chestertown Maryland
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About Chestertown
Chestertown has total households of 8,375 with a real estate for sale median home value of $291,900 compared to the state median home price of $411,900. The median real estate taxes paid are $Not Available and the household income is $71,635. Not Available% of Chestertown homes with a mortgage have no second mortgage or home equity line of credit. Chestertown Maryland home types of MLS housing to buy including single family homes, condos, townhomes, residential studio, apartment, townhouse, and multi-family houses.
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Housing Disclaimer: Certain information contained herein is derived from information provided by parties other than Airdeed.com. All information provided is deemed reliable, but is not guaranteed to be accurate and users should independently verify all information.
Chestertown Community Map
§ 442-H New York Standard Operating Procedures
TREC: Consumer protection notice
HUD: Equal Opportunity Housing